Triallyl ethers of dioxaborinane



United States Patent "ice 3325528 Patented June 13, 1967 an excessively slow reaction rate. The water can also be 3,325,528 removed by refluxing the reaction mixture in the presence TRIALLYL ETHERS 0F DIOXABORINANE Richard B. Lund, Whippany, and Arleen C. Pierce, Parsippany, N.J., assignors to Allied Chemical Corporaof an inert drying agent such as magnesium sulfate.

The monoallyl ethers of dioxaborinane used as reactants 5 in the present invention can be prepared from boric acid g "f g a z fi g g fg and an allyloxy-substituted dihydric alcohol, in accord- '2 Claims. ((31. 260 462) ance with the following equation:

This invention relates to novel borinane compounds 1 1 1 and the preparation thereof. More particularly this inven- 10 CI}H=O ..C|}H O .CH2 JJ CH2OH tion relates to triallyl ethers of dioxaborinane and a process for their preparation. CH2OH The triallyl ethers of dioxaborinane within the scope R CHPO of the present invention are represented by the following CH=O-oH0oHi--i BOH 2H20 formula: OHPO R1 R1 R1 wherein R and R have the meanings given above. The water formed in this reaction should be removed. It is CH:C CH*O(|3H CHM) f f R1 R1 not necessary to isolate the resulting monoallyl ether of RC B-o-onio-ong-o-on-o=on dioxaborinane, but rather after the boric acid and allyloxy CHrO CHHFCEPCZCH substituted dihydric alcohol have reacted, the 1,3-dial- 1 1 1 lyloxy-2-alkyl-2-hydroxymethylpropane used to produce the compounds of the invention can be added directly to the reaction mixture. wherein each R is independently an alkyl group which The following COITlpOlJIldS are illustrative Of the novel f bl t i 1 5 carbon w d h R i i triallyl ethers of dioxaborinane of the present invention: dependently a group selected from the class consisting Z 3 diallyloxymethyl P P Y) 5 allyloXymeth' of hydrogen and alkyl groups, the latter of which prefer- Y 5 ethyl 1,3,2 diOXabOfiIlaIle; 2 y Y' ably contains 1-5 carbon atoms. These compounds are methyl Y) 5 anyloxymethyl 5 ethyl 1,3,2 useful as stabilizers for polymeric compositions against the OXabOfinane; Y Y y Y)- Y effect of elevated temperatures, and are particularly etfecoXymethyl 5 butyl 1,3,2 diOXflbOriHaHe; 2 '3 tive as stabilizers for chlorinated organic compounds. biS(1,2,3 tfimdhylallyloxymethyl) Y] 5 y y- It is therefore an object of the present invention to promethyhiethyh1,3,2-di0Xab0fiIlane; and vide novel borinane compounds and a method for their 3 trimethylallyloXymethyl)blltOXY] 5 'Erimethpreparation. ylallyloxymet'hyl) 5 ethyl 1,3,2 dioxaborinane. The

Another object of the present i ntio i t id above listed compounds are merely given for illustrativenove1tria11y1 ther f dio abo i an purposes, and it will be obvious that many additional Additional objects and advantages of this invention CPmPOIIHdS are Within the Scope of the Present Invenwill become apparent from the following detailed detlOnscription thereof, 40 The compounds of the present invention can be used for In accordance with the present invention novel triallyl the Stabilization of POIYmeTiC composition? against the ethers of dioxaborinane are prepared by the reaction of a effect of elevated tempeffltllfes, and a partlcularly effecmonoallyl ether of dioxaborinane with a 1,3-diallyloxy-2- tlve 1n stabilizing chlorinated organic compounds, such alkyl-Z-hydroxymethylpropane as illustrated in the followas chlorinated polyethylene. When used as stabilizers for ing equation: chlorinated polyethylene, the dioxaborinane compounds R1 $1 i i /CHz0 R1 1 R1 II 1 i i R1 H=CCHOCH- -(g BOH CH=C-H-OCH2CCH2OCHC=H wherein R and R have the meanings given above. The of this invention should be added to the polymer in amount water formed in the reaction should be removed or the equal to at least 0.5% by weight of the polymer and pre'freaction will not go to completion. The water can be diserably in an amount equal to about 1.0-l0% by Weight tilled ofr' by conducting the reaction at a temperature of of the polymer. In a typical example it was found that the at least 100 C. or by carrying out the reaction at reflux addition to chlorinated polyethylene of 4% by Weight of temperature in a solvent which forms an azeotropic mix- 2 (2',2' diallyloxymethyl butoxy) 5 allyloxymethylture with water. If a solvent is used, itshould, of course, S-ethyl-l,3,2-dioxaborinane substantially decreased the not interfere with the reaction and it should preferably crosslinking of the polymer resulting from treatment at have a boiling point of at least C. in order to avoid 200 C. for 1 hour.

The following example is given to further illustrate the invention, but it is to be understood that the invention is not to be limited in any way by the detailed description therein.

Example 17.4 parts by weight trimethylolpropane monoallyl ether were mixed with 6.2 parts by Weight boric acid and heated under reflux until 3.6 parts by weight water were collected in a Dean Stark trap. There was then added to the reaction mixture 21.4 parts by weight trimethylolpropane diallyl ether and heating was continued until the reaction subsided. The product thus produced was confirmed to be 2 (2',2 diallyloxymethyl butoxy) 5 allyloxymethyl-S-ethyld,3,2-dioxaborinane, by its infrared spectrum.

It will be apparent that many modifications and variations may be effected without departing from the scope of the novel concepts of the present invention, and the illustrative details disclosed are not to be construed as imposing undue limitations on the invention.

We claim:

1. A compound of the formula:

References Cited UNITED STATES PATENTS 2,994,713 8/1961 Lane 260462 CHARLES B. PARKER, Primary Examiner.

DELBERT R. PHILLIPS, Assistant Examiner. 

1. A COMPOUND OF THE FORMULA: 